Diaqua-bromido-copper(II)-18-crown-6-water (1/1/2).

In the title compound, [CuBr(2)(H(2)O)(2)]·C(12)H(24)O(6)·2H(2)O, the Cu(II) atom, which is situated on an inversion centre and has a slightly distorted square-planar geometry, and the two coordinated water mol-ecules are linked to the 18-crown-6 macrocycles by O-H⋯O hydrogen bonds. The water mol-ecule of crystallization further links the metal complex and the crown ether macrocycles into a chain along the c axis.

Related literature

For the ability of 18-crown-6 ether to form complexes with different metal ions, see: Jackson et al. (1981 ▶); Otter & Hartshorn (2004 ▶). For similar structures, see: Antsyshkina et al. (2004 ▶); Liu et al. (2007 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

[CuBr2(H2O)2]·C12H24O6·2H2O

M = 559.73

Triclinic,

a = 7.4418 (5) Å

b = 8.1724 (6) Å

c = 10.1510 (2) Å

α = 75.220 (3)°

β = 69.47 (1)°

γ = 78.51 (1)°

V = 554.90 (6) Å3

Z = 1

Mo Kα radiation

μ = 4.63 mm−1

T = 298 K

0.20 × 0.20 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan CrystalClear (Rigaku, 2005 ▶) T min = 0.397, T max = 0.412

5746 measured reflections

2537 independent reflections

2064 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.155

S = 1.08

2537 reflections

123 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.27 e Å−3

Δρmin = −1.55 e Å−3

Data collection: CrystalClear (Rigaku 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: PRPKAPPA (Ferguson, 1999 ▶).

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536810023500/jj2036sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810023500/jj2036Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[CuBr2(H2O)2]·C12H24O6·2H2O	Z = 1
Mr = 559.73	F(000) = 283
Triclinic, P1	Dx = 1.675 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4418 (5) Å	Cell parameters from 2622 reflections
b = 8.1724 (6) Å	θ = 3.0–27.5°
c = 10.1510 (2) Å	µ = 4.63 mm−1
α = 75.220 (3)°	T = 298 K
β = 69.47 (1)°	Prism, green
γ = 78.51 (1)°	0.20 × 0.20 × 0.20 mm
V = 554.90 (6) Å3

Rigaku SCXmini diffractometer	2537 independent reflections
Radiation source: fine-focus sealed tube	2064 reflections with I > 2σ(I)
graphite	Rint = 0.037
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.0°
ω scans	h = −9→9
Absorption correction: multi-scan CrystalClear (Rigaku, 2005)	k = −10→10
Tmin = 0.397, Tmax = 0.412	l = −13→13
5746 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.155	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0755P)2 + 0.8701P] where P = (Fo2 + 2Fc2)/3
2537 reflections	(Δ/σ)max < 0.001
123 parameters	Δρmax = 1.27 e Å−3
0 restraints	Δρmin = −1.55 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Br1	0.05334 (10)	0.20118 (6)	0.58028 (6)	0.0652 (3)
C1	0.7159 (11)	0.5878 (10)	0.2213 (9)	0.080 (2)
H1A	0.7893	0.5678	0.2875	0.096*
H1B	0.5881	0.6430	0.2652	0.096*
C2	0.6378 (11)	0.3049 (11)	0.3232 (7)	0.082 (2)
H2A	0.5237	0.3535	0.3903	0.099*
H2B	0.7387	0.2700	0.3681	0.099*
C3	0.5931 (11)	0.1552 (9)	0.2897 (7)	0.078 (2)
H3A	0.7043	0.1104	0.2180	0.094*
H3B	0.5624	0.0664	0.3755	0.094*
C4	0.3741 (11)	0.0667 (7)	0.2063 (8)	0.077 (2)
H4A	0.3196	−0.0119	0.2951	0.092*
H4B	0.4851	0.0053	0.1465	0.092*
C5	0.2298 (10)	0.1320 (9)	0.1320 (9)	0.079 (2)
H5A	0.1834	0.0378	0.1166	0.095*
H5B	0.1206	0.1968	0.1901	0.095*
C6	0.1858 (10)	0.3000 (10)	−0.0843 (10)	0.083 (2)
H6A	0.0709	0.3637	−0.0304	0.100*
H6B	0.1466	0.2052	−0.1045	0.100*
Cu1	0.0000	0.5000	0.5000	0.0335 (2)
O1	0.7004 (6)	0.4308 (6)	0.1941 (4)	0.0626 (10)
O2	0.4337 (5)	0.2051 (5)	0.2370 (4)	0.0559 (9)
O3	0.3148 (5)	0.2374 (5)	−0.0014 (5)	0.0613 (10)
O4W	0.3072 (6)	0.6708 (6)	0.0637 (4)	0.0566 (10)
O5W	0.1698 (7)	0.4741 (5)	0.3133 (4)	0.0900 (18)
H5WA	0.2229	0.3756	0.2979	0.108*
H5WB	0.1920	0.5610	0.2455	0.108*
H4WA	0.309 (11)	0.633 (10)	0.011 (8)	0.07 (3)*
H4WB	0.436 (11)	0.688 (9)	0.040 (8)	0.08 (2)*

	U11	U22	U33	U12	U13	U23
Br1	0.0949 (5)	0.0358 (3)	0.0446 (3)	−0.0137 (3)	0.0039 (3)	−0.0051 (2)
C1	0.085 (5)	0.091 (5)	0.092 (5)	0.007 (4)	−0.054 (4)	−0.043 (4)
C2	0.088 (5)	0.112 (6)	0.044 (3)	0.010 (4)	−0.035 (3)	−0.007 (4)
C3	0.088 (5)	0.066 (4)	0.053 (4)	0.011 (4)	−0.016 (3)	0.011 (3)
C4	0.093 (5)	0.037 (3)	0.066 (4)	−0.015 (3)	0.016 (4)	−0.006 (3)
C5	0.066 (4)	0.059 (4)	0.095 (5)	−0.033 (3)	0.015 (4)	−0.025 (4)
C6	0.066 (4)	0.084 (5)	0.132 (7)	−0.008 (4)	−0.045 (5)	−0.057 (5)
Cu1	0.0319 (4)	0.0385 (4)	0.0250 (4)	−0.0049 (3)	−0.0047 (3)	−0.0033 (3)
O1	0.068 (2)	0.077 (3)	0.048 (2)	0.000 (2)	−0.023 (2)	−0.022 (2)
O2	0.056 (2)	0.0428 (19)	0.047 (2)	0.0025 (16)	0.0013 (17)	−0.0033 (16)
O3	0.049 (2)	0.060 (2)	0.073 (3)	−0.0165 (18)	−0.0070 (19)	−0.021 (2)
O4W	0.054 (2)	0.074 (3)	0.034 (2)	−0.016 (2)	−0.0026 (17)	−0.0073 (19)
O5W	0.109 (4)	0.054 (2)	0.040 (2)	0.029 (2)	0.026 (2)	0.0074 (18)

Br1—Cu1	2.3687 (5)	C4—H4B	0.9700
C1—O1	1.414 (8)	C5—O3	1.413 (8)
C1—C6i	1.488 (11)	C5—H5A	0.9700
C1—H1A	0.9700	C5—H5B	0.9700
C1—H1B	0.9700	C6—O3	1.429 (8)
C2—O1	1.438 (8)	C6—C1i	1.488 (11)
C2—C3	1.476 (11)	C6—H6A	0.9700
C2—H2A	0.9700	C6—H6B	0.9700
C2—H2B	0.9700	Cu1—O5Wii	1.911 (4)
C3—O2	1.414 (8)	Cu1—O5W	1.911 (4)
C3—H3A	0.9700	Cu1—Br1ii	2.3687 (5)
C3—H3B	0.9700	O4W—H4WA	0.68 (7)
C4—O2	1.432 (8)	O4W—H4WB	0.93 (8)
C4—C5	1.463 (11)	O5W—H5WA	0.8500
C4—H4A	0.9700	O5W—H5WB	0.8500
O1—C1—C6i	109.7 (6)	O3—C5—H5A	109.9
O1—C1—H1A	109.7	C4—C5—H5A	109.9
C6i—C1—H1A	109.7	O3—C5—H5B	109.9
O1—C1—H1B	109.7	C4—C5—H5B	109.9
C6i—C1—H1B	109.7	H5A—C5—H5B	108.3
H1A—C1—H1B	108.2	O3—C6—C1i	109.5 (5)
O1—C2—C3	110.2 (5)	O3—C6—H6A	109.8
O1—C2—H2A	109.6	C1i—C6—H6A	109.8
C3—C2—H2A	109.6	O3—C6—H6B	109.8
O1—C2—H2B	109.6	C1i—C6—H6B	109.8
C3—C2—H2B	109.6	H6A—C6—H6B	108.2
H2A—C2—H2B	108.1	O5Wii—Cu1—O5W	180.000 (1)
O2—C3—C2	108.9 (5)	O5Wii—Cu1—Br1ii	89.03 (12)
O2—C3—H3A	109.9	O5W—Cu1—Br1ii	90.97 (12)
C2—C3—H3A	109.9	O5Wii—Cu1—Br1	90.97 (12)
O2—C3—H3B	109.9	O5W—Cu1—Br1	89.03 (12)
C2—C3—H3B	109.9	Br1ii—Cu1—Br1	180.0
H3A—C3—H3B	108.3	C1—O1—C2	112.9 (6)
O2—C4—C5	109.9 (5)	C3—O2—C4	113.2 (5)
O2—C4—H4A	109.7	C5—O3—C6	112.7 (5)
C5—C4—H4A	109.7	H4WA—O4W—H4WB	103 (8)
O2—C4—H4B	109.7	Cu1—O5W—H5WA	120.0
C5—C4—H4B	109.7	Cu1—O5W—H5WB	120.0
H4A—C4—H4B	108.2	H5WA—O5W—H5WB	120.0
O3—C5—C4	109.1 (5)
O1—C2—C3—O2	−64.8 (7)	C2—C3—O2—C4	−177.8 (5)
O2—C4—C5—O3	63.1 (7)	C5—C4—O2—C3	−171.2 (5)
C6i—C1—O1—C2	169.8 (6)	C4—C5—O3—C6	177.1 (5)
C3—C2—O1—C1	170.5 (6)	C1i—C6—O3—C5	178.9 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O4W—H4WA···O1i	0.68 (7)	2.30 (8)	2.962 (6)	167 (9)
O4W—H4WB···O3i	0.93 (8)	1.95 (8)	2.869 (6)	170 (6)
O5W—H5WA···O2	0.85	1.92	2.715 (5)	156
O5W—H5WB···O4W	0.85	1.82	2.609 (6)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4W—H4WA⋯O1i	0.68 (7)	2.30 (8)	2.962 (6)	167 (9)
O4W—H4WB⋯O3i	0.93 (8)	1.95 (8)	2.869 (6)	170 (6)
O5W—H5WA⋯O2	0.85	1.92	2.715 (5)	156
O5W—H5WB⋯O4W	0.85	1.82	2.609 (6)	155

Symmetry code: (i) .